Synthesis of Polycyclic Chromene Cores through Gold (I)-Catalyzed Intramolecular Hydroarylation Reaction (IMHA)

被引：10

作者：

Arcadi, Antonio ^{[1
]}

Fabrizi, Giancarlo ^{[2
]}

Fochetti, Andrea ^{[2
]}

Franzini, Roberta ^{[2
]}

Ghirga, Francesca ^{[3
]}

Goggiamani, Antonella ^{[2
]}

Iazzetti, Antonia ^{[2
]}

Marrone, Federico ^{[2
]}

Serraiocco, Andrea ^{[2
]}

机构：

[1] Univ Aquila, Dipartimento Sci Fis & Chim, Via Vetoio, I-67100 Coppito, AQ, Italy

[2] Sapienza Univ Roma, Dipartimento Chim & Tecnol Farmaco, Ple A Moro 5, I-00185 Rome, Italy

[3] Ist Italiano Tecnol, Ctr Life Nano Sci Sapienza, Viale Regina Elena 291, I-00161 Rome, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 11期

关键词：

Annulation; Gold catalysis; Hydroarylation; CATALYZED HYDROARYLATION; ALKYNES;

D O I：

10.1002/ejoc.202100092

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regioselective gold (I)-catalyzed approach for the construction of polycyclic chromene cores has been developed. The reaction proceeds in good to excellent yields under mild condition with a broad range of substrates providing a simple and efficient tool for the synthesis of pyranochromene derivatives. Moreover, the regiochemical control of the annulation of unsymmetrically substituted propargylic ethers has been investigated focusing on electronic/steric effects of the ligands of gold complexes as well as on the electronic effects of the groups on the aromatic rings.

引用

页码：1676 / 1687

页数：12

共 36 条

[1] Multiaddressable self-assembling organogelators based on 2H-chromene and N-acyl-1,ω-amino acid units
Ahmed, SA
Sallenave, X
Fages, F
Mieden-Gundert, G
Müller, WM
Müller, U
Vögtle, F
Pozzo, JL
[J]. LANGMUIR, 2002, 18 (19) : 7096 - 7101
[2] Synthesis of pyrano[2,3-f]chromen-2-ones vs. pyrano[3,2-g]chromen-2-ones through site controlled gold-catalyzed annulations
Arcadi, Antonio
Ciogli, Alessia
Fabrizi, Giancarlo
Fochetti, Andrea
Franzini, Roberta
Ghirga, Francesca
Goggiamani, Antonella
Iazzetti, Antonia
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (47) : 10065 - 10072
[3] Gold versus silver catalyzed intramolecular hydroarylation reactions of [(3-arylprop-2-ynyl)oxy]benzene derivatives
Arcadi, Antonio
Blesi, Federico
Cacchi, Sandro
Fabrizi, Giancarlo
Goggiamani, Antonella
Marinelli, Fabio
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (48) : 9700 - 9708
[4] Microwave-assisted synthesis of 10-aryl-4-methyl-2-oxo-8-phenyl-2,8-dihydropyrano[2,3-f]chromene-9-carbaldehydes by Suzuki coupling and their antimicrobial activity
Ashok, Dongamanti
Lakshmi, Bommidi Vijaya
Ravi, Sidda
Ganesh, Arram
Adam, Shaik
[J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2015, 51 (05) : 462 - 466
[5] Intramolecular iodoarylation reaction of alkynes:: easy access to derivatives of benzofused heterocycles
Barluenga, J
Trincado, M
Marco-Arias, M
Ballesteros, A
Rubio, E
González, JM
[J]. CHEMICAL COMMUNICATIONS, 2005, (15) : 2008 - 2010
[6] Gold-Catalyzed Carbon-Heteroatom Bond-Forming Reactions
Corma, A.
Leyva-Perez, A.
Sabater, Maria J.
[J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1657 - 1712
[7] A facile gold(I)-catalysed intramolecular alkyne hydroarylation approach to methyl 5-amino-2H-1-benzopyran-8-carboxylate derivatives
Curtis, Neil R.
Prodger, Jeremy C.
Rassias, Geracimos
Walker, Andrew J.
[J]. TETRAHEDRON LETTERS, 2008, 49 (44) : 6279 - 6281
[8] Synthesis of arenes and heteroarenes by hydroarylation reactions catalyzed by electrophilic metal complexes
de Mendoza, Paula
Echavarren, Antonio M.
[J]. PURE AND APPLIED CHEMISTRY, 2010, 82 (04) : 801 - 820
[9] Utility of Ligand Effect in Homogenous Gold Catalysis: Enabling Regiodivergent π-Bond-Activated Cyclization
Ding, Dong
Mou, Tao
Feng, Minghao
Jiang, Xuefeng
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (16) : 5218 - 5221
[10] From Palladium to Gold Catalysis for the Synthesis of Crushed Fullerenes and Acenes
Dorel, Ruth
Echavarren, Antonio M.
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2019, 52 (07) : 1812 - 1823

← 1 2 3 4 →